Josh Sklar – Product & Engineering Leader

About

I started my career as a software engineer. I loved building things, but I kept finding myself more interested in why we were building them than how. That instinct eventually pulled me into product.

I joined StockX in 2016 as the 19th employee and spent eight and a half years there, building the iOS app and eventually leading product for parts of the consumer purchasing experience – product discovery, research, and catalog.

Since then, I’ve led product at early-stage startups, working across the full stack of what it means to run product: strategy, roadmaps, analytics, hiring, and the hard conversations that come with building in constrained environments.

I care a lot about craft. Good product work, to me, looks a lot like good writing – clear thinking made visible. I’m drawn to problems where the stakes are real and the feedback loops are tight.

Outside of work, I spend a lot of time outdoors. I’ve completed six Ironman 70.3s, two marathons, and a bunch of half marathons. I play piano and love to make mixed-media art pieces. My amazing fiancée even let me hang one up right in our kitchen. I’m Jewish and active in the NYC Jewish community. I currently live in NYC, but was born and raised in Michigan.

Career

A few of the places I’ve worked and what I did there.

Jolly→

SVP of Product

Led product for a B2B2C SaaS workforce performance optimization platform that helped frontline workers earn a stake in the outcomes they drive and feel more connected to their companies. Drove a full platform rebuild.

Pickle→

Head of Product

Joined as the 12th employee. Led product for a peer-to-peer clothing rental marketplace. Drove initiatives to increase offer acceptance rate, click-through rate, and order conversion rate.

StockX→

Lead Product Manager

Joined as the 19th employee. Built the iOS app, led engineering teams, and ran product for parts of the consumer purchasing experience – product discovery, research, and catalog.

Earlier

Software Engineer · Various Companies

Worked as a software engineer before moving into product full-time, shipping apps for Fortune 500 clients including Domino’s Pizza and KIA Motors. That foundation still shapes how I think about technical tradeoffs and what’s actually hard to build.

What Others Say

Your decision documents are absolutely award winning gold medal type stuff. Clear approvals, very clear guidance on options considered. The little plus and minus signs, and everything.

Chief Product Officer

In my past, I’ve seen Product Managers not take an easy quick-win from their predecessor PM because they want to do their own thing or some other ego-driven reason. Josh on the other hand asked questions, identified the opportunity, and launched it. I love that behavior.

VP of Product

Both in engineering and in product, you’ve been someone I trusted, relied upon, and had the utmost faith that you would figure it out. Further, I really appreciate your level headedness, your ability to communicate with the team, and your constant desire to grow.

Product Marketing Manager

Your decision documents are absolutely award winning gold medal type stuff. Clear approvals, very clear guidance on options considered. The little plus and minus signs, and everything.

Chief Product Officer

In my past, I’ve seen Product Managers not take an easy quick-win from their predecessor PM because they want to do their own thing or some other ego-driven reason. Josh on the other hand asked questions, identified the opportunity, and launched it. I love that behavior.

VP of Product

Both in engineering and in product, you’ve been someone I trusted, relied upon, and had the utmost faith that you would figure it out. Further, I really appreciate your level headedness, your ability to communicate with the team, and your constant desire to grow.

Product Marketing Manager

Outside of work, you’ve been an inspiration for me — whether it’s been moonlighting as a B school student, the races and physical challenges you’ve put yourself through and overcame, or just your open embrace and friendship. I hope that I can take your lessons and embody them for the rest of my life.

Product Marketing Manager

Josh really shined during our UX reviews with detail-oriented feedback and reasoning backed by historical data results, all of which helped us to keep challenging funnel points driving forward. I enjoyed Josh’s enthusiasm for the industry and always walked away from our conversations with new perspectives.

Lead Product Designer

One of Josh’s standout qualities is his exceptional skill in crafting well-written, comprehensive documents that communicate ideas and strategies with unparalleled clarity. Josh played a key role in shaping the Product Pages on StockX and solving complex All-in Ask challenges by collaborating seamlessly with cross-functional teams. His strategic thinking, authenticity, and his ability to “say it as it is” ensures that teams are aligned and focused on the right priorities.

Lead Product Manager

Outside of work, you’ve been an inspiration for me — whether it’s been moonlighting as a B school student, the races and physical challenges you’ve put yourself through and overcame, or just your open embrace and friendship. I hope that I can take your lessons and embody them for the rest of my life.

Product Marketing Manager

Josh really shined during our UX reviews with detail-oriented feedback and reasoning backed by historical data results, all of which helped us to keep challenging funnel points driving forward. I enjoyed Josh’s enthusiasm for the industry and always walked away from our conversations with new perspectives.

Lead Product Designer

One of Josh’s standout qualities is his exceptional skill in crafting well-written, comprehensive documents that communicate ideas and strategies with unparalleled clarity. Josh played a key role in shaping the Product Pages on StockX and solving complex All-in Ask challenges by collaborating seamlessly with cross-functional teams. His strategic thinking, authenticity, and his ability to “say it as it is” ensures that teams are aligned and focused on the right priorities.

Lead Product Manager

Josh has an extraordinary ability to envision and deliver world-class customer experiences. He has a meticulous approach to documentation and creates artifacts that are both clear and actionable—something that made working with him as an engineer seamless and efficient. Josh excels at aligning diverse inputs from design, engineering, and business teams into a cohesive product vision. His ability to synthesize ideas and drive alignment made even the most complex projects feel manageable.

Senior Engineering Manager

Josh demonstrated a deep understanding of market trends and customer needs. His people skills are unparalleled, enabling him to lead and inspire. What really sets Josh apart is his strategic use of questioning to drive innovation, as he consistently challenges assumptions and explores new perspectives to push the boundaries of what’s possible. Josh is not just an exceptional Product Leader but an even better person whom I would highly recommend.

Business Operations Manager

Josh has an extraordinary ability to envision and deliver world-class customer experiences. He has a meticulous approach to documentation and creates artifacts that are both clear and actionable—something that made working with him as an engineer seamless and efficient. Josh excels at aligning diverse inputs from design, engineering, and business teams into a cohesive product vision. His ability to synthesize ideas and drive alignment made even the most complex projects feel manageable.

Senior Engineering Manager

Josh demonstrated a deep understanding of market trends and customer needs. His people skills are unparalleled, enabling him to lead and inspire. What really sets Josh apart is his strategic use of questioning to drive innovation, as he consistently challenges assumptions and explores new perspectives to push the boundaries of what’s possible. Josh is not just an exceptional Product Leader but an even better person whom I would highly recommend.

Business Operations Manager

Writing

I write about product, design, and leadership. Most of it lives on LinkedIn.

Josh Sklar

March 6, 2025

I used to work with someone who almost every time they wanted to communicate something, they’d send a Slack DM. Stop doing this. Default to public channels instead. Here’s why...

4,328 likes305 comments

Product and engineering leader. Passionate about people-first culture. 14+ years of building and scaling consumer apps.

Jolly→

Pickle→

StockX→

Earlier